US3732196A - Anti-electrostatic light-stable polyolefin moulding compositions - Google Patents
Anti-electrostatic light-stable polyolefin moulding compositions Download PDFInfo
- Publication number
- US3732196A US3732196A US00110777A US3732196DA US3732196A US 3732196 A US3732196 A US 3732196A US 00110777 A US00110777 A US 00110777A US 3732196D A US3732196D A US 3732196DA US 3732196 A US3732196 A US 3732196A
- Authority
- US
- United States
- Prior art keywords
- electrostatic
- moulding compositions
- agents
- light
- mouldings
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000465 moulding Methods 0.000 title abstract description 22
- 229920000098 polyolefin Polymers 0.000 title abstract description 19
- 239000000203 mixture Substances 0.000 title abstract description 14
- 239000002216 antistatic agent Substances 0.000 abstract description 17
- 150000003839 salts Chemical class 0.000 abstract description 16
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract description 2
- 229940035437 1,3-propanediol Drugs 0.000 abstract description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- -1 polyethylene Polymers 0.000 description 13
- 239000004698 Polyethylene Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000007600 charging Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 238000007792 addition Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 1
- XKQMKMVTDKYWOX-UHFFFAOYSA-N 1-[2-hydroxypropyl(methyl)amino]propan-2-ol Chemical compound CC(O)CN(C)CC(C)O XKQMKMVTDKYWOX-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019383 crystalline wax Nutrition 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 238000007786 electrostatic charging Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000570 polyether Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
- Y10S260/19—Non-high polymeric antistatic agents/n
- Y10S260/20—Antistatic agent contains pentavalent nitrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/91—Antistatic compositions
- Y10S524/913—Contains nitrogen nonreactant material
Definitions
- This invention relates to anti-electrostatic, stable moulding compositions based on olefin homopolymers and copolymers.
- mouldings obtained from olefin polymers can readily become electrostatically charged, with the result that they attract dust particles, which adversely affect both the appearance and the quality of the mouldings.
- mouldings of large surface area excessive charging and contact can actually be accompanied by charge equalisation through spark discharge. For this reason, there has been many attempts to find agents which reduce or prevent the undesirable electrostatic charging of mouldings.
- hydrophobic radicals are long-chain alkyl groups.
- hydrophilic radicals can be, for example, hydroxy groups, polyether groups or salt groups (cf. German Auslegeschrifts Nos. 1,248,932, 1,247,010 and 1,247,009).
- the objects of the present invention was to provide antistatic agents for polyolefin compositions which are stable both to heat and light and which do not necessitate any further additions of stabilisers.
- the antielectrostatic agents should be physiologically acceptable.
- this object is achieved by using salts of fatty acids with 1,3-diols containing a dialkylamino group attached through a methylene group in the 2-position, as anti-electrostatic agents.
- the invention relates to an anti-electrostatic light-stable moulding composition based on an olefin polymer, and optionally containing fillers, plasticisers, pigments, lubricants and soluble dyes, which contain, as antistatic agent a salt having the Formula I R: CHzOH l e-om 011.011 4 in which In the above formula, R and R preferably represent CH R represents CH or C H and R represents C C alkyl or C -alkenyl (oleyl).
- the antistatically-active salt is added to the moulding composition preferably in a quantity of from 0.03 to 2% by weight, and especially in a quantity of from 0.05 to 1% by weight, based on the olefin polymer. It is of course also possible to use mixtures of the aforementioned salts.
- polymers include homopolymers of olefins, copolymers of at least one olefin and at least one other copolymerisable monomer with a proportion of at least 50% by weight of an olefin, as well as mixtures of the aforementioned homopolymers and copolymers.
- polyethylene polypropylene, polybutene, poly-4-methyl-1- pentene
- ethylene-propylene copolymers ethylene-butene copolymers
- ethylene-hexene copolymers ethylene-vinyl acetate copolymers
- ethylene-vinyl chloride copolymers polyolefin ionomers, and polyallomers etc.
- Polyethylene and polypropylene are preferred, polyethylene being particularly preferred.
- the new antistatic agents can be prepared simply by combmmg tert.-aminodiols (cf. British patent application 61/298,168) corresponding to the general formula and fatty acids of the general formula R COO'H, in which R -R have the meanings given above, preferably at temperatures above the melting point of the carboxylic acids used or even at temperatures of from 10 to 40 0., providing the salts formed are liquid at temperatures in this range.
- the solid carboxylic acid may simply be dissolved in the liquid aminodiol at room temperature.
- Saturated carboxylic acids whose hydrocarbon radical contains 10 to 18 carbon atoms, are particularly preferred.
- the salts formed are, in some instances relatively mobile, colourless oils which can readily be added, applied to or introduced into the olefin polymers and processed. Whereas most salts remain mobile even after prolonged storage, the stearates solidify to form crystalline waxes. Even in the event of prolonged storage in light, there are no signs of yellowing, in contrast to what is observed with corresponding salts of hydroxy ethylated amines.
- the antistatic agents used in accordance with the invention may optionally be Worked into the polyolefins simultaneously with the incorporation of the conventional additives, such as pigments, soluble dyes, plasticisers, and lubricants, does not present any difiiculties, nor does it necessitate the use of solvents of suspending agents. It can be carried out by direct addition during preparation of a granulate, or during moulding in conventional processing apparatus.
- the conventional additives such as pigments, soluble dyes, plasticisers, and lubricants
- the products do not show any signs of decomposition or discolouration, even at relatively high or excessively high processing temperatures, for example in the range from 240 to 260 'C., or during prolonged residence periods in the processing apparatus; more particularly no water is given off as is possible through amidation reactions if secondary and primary amines are used.
- the advantage of the anti-electrostatic agents used in accordance with the invention lies in the very fact that there is no need to add stabilisers, the conventional stabilisers may optionally be used in order to prevent yellowing.
- the antistatic agents in a suitable readily volatile organic solvent, such as a Example lower alcohol, for example methanol or ethanol, to add the solution or suspension thus obtained to the polyolefin, and then to remove the solvent by distillation.
- a suitable readily volatile organic solvent such as a Example lower alcohol, for example methanol or ethanol
- the finished plastics mouldings based on the polyolefins can also be surface-treated by dipping or spraying with a dilute aqueous or organic solution of the anti-electrostatic agents.
- the mouldings according to the invention can be injection-moulded to form mouldings of any type by known methods, such as blow-moulding, rolling or pressing etc.
- the mouldings do not show any signs of yellowing, either under the influence of light or of that of heat, and show outstanding anti-electrostatic properties.
- the anti-elec trostatic agents did not show any tendency towards exudation, which is of particular advantage in the production of films.
- the anti-electrostatic agents used in accordance with the invention are largely acceptable from the physiological point of view.
- the rolled sheets obtained were granulated and moulded into panels measuring 120 x 120 x 4 mm. (low-pressure heating time 5 minutes, high-pressure moulding time 5 minutes, cooling time 10 minutes).
- a moulding composition which comprises an olefin polymer and an antistatic efiective amount of a compound of the formula R3 CHzOH wherein R is CH or C H R is al'kyl having from 1 to 18 carbon atoms or R and R when taken together arealkylene having from 4 to 6 carbon atoms, R is alkyl having from 1 to 6 carbon atoms and R is alkyl or alkenyl containing from 5 to 22 carbon atoms.
- the antistatic agent is a compound of said formula wherein R and R are methyl, R is methyl or ethyl, and R is oleyl or alkyl having from 10 to 18 carbon atoms.
- the moulding composition of claim 1 wherein the antistatic agent is the dodecanoic acid salt of Z-dimethylaminomethyl-2-ethyl-1,3-propane diol.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702010118 DE2010118A1 (de) | 1970-03-04 | 1970-03-04 | Antielektrostatische, lichtstabile Polyolefinformmassen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3732196A true US3732196A (en) | 1973-05-08 |
Family
ID=5764040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00110777A Expired - Lifetime US3732196A (en) | 1970-03-04 | 1971-01-28 | Anti-electrostatic light-stable polyolefin moulding compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3732196A (xx) |
| BE (1) | BE763793A (xx) |
| DE (1) | DE2010118A1 (xx) |
| FR (1) | FR2084202A5 (xx) |
| GB (1) | GB1300341A (xx) |
| NL (1) | NL7102837A (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922249A (en) * | 1973-04-12 | 1975-11-25 | Phillips Petroleum Co | Stabilized antistatic compositions useful with olefin polymers |
| US5153075A (en) * | 1988-01-14 | 1992-10-06 | W. R. Grace & Co.-Conn. | Permanent antistatic acid copolymer/quaternary amine polymeric films |
| US5171641A (en) * | 1988-01-14 | 1992-12-15 | W. R. Grace & Co.-Conn. | Permanent antistatic acid copolymer/quaternary amine polymeric films |
-
1970
- 1970-03-04 DE DE19702010118 patent/DE2010118A1/de active Pending
-
1971
- 1971-01-28 US US00110777A patent/US3732196A/en not_active Expired - Lifetime
- 1971-03-03 NL NL7102837A patent/NL7102837A/xx unknown
- 1971-03-04 FR FR7107511A patent/FR2084202A5/fr not_active Expired
- 1971-03-04 BE BE763793A patent/BE763793A/xx unknown
- 1971-04-19 GB GB21702/71A patent/GB1300341A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922249A (en) * | 1973-04-12 | 1975-11-25 | Phillips Petroleum Co | Stabilized antistatic compositions useful with olefin polymers |
| US5153075A (en) * | 1988-01-14 | 1992-10-06 | W. R. Grace & Co.-Conn. | Permanent antistatic acid copolymer/quaternary amine polymeric films |
| US5171641A (en) * | 1988-01-14 | 1992-12-15 | W. R. Grace & Co.-Conn. | Permanent antistatic acid copolymer/quaternary amine polymeric films |
Also Published As
| Publication number | Publication date |
|---|---|
| BE763793A (fr) | 1971-08-02 |
| DE2010118A1 (de) | 1971-09-23 |
| NL7102837A (xx) | 1971-09-07 |
| GB1300341A (en) | 1972-12-20 |
| FR2084202A5 (xx) | 1971-12-17 |
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